Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-Sphinganine, (+)-spisulosine and D-ribo-phytosphingosine

Calder, E.D.D., Zaed, A.M. and Sutherland, A. (2013) Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-Sphinganine, (+)-spisulosine and D-ribo-phytosphingosine. Journal of Organic Chemistry, 78(14), pp. 7223-7233. (doi: 10.1021/jo401211j)

Abstract

Two variations of the Overman rearrangement have been developed for the highly selective synthesis of anti-vicinal amino alcohol natural products. A MOM-ether directed palladium(II)-catalyzed rearrangement of an allylic trichloroacetimidate was used as the key step for the preparation of the protein kinase C inhibitor D-erythro-sphinganine and the antitumor agent (+)-spisulosine, while the Overman rearrangement of chiral allylic trichloroacetimidates generated by asymmetric reduction of an alpha,beta-unsaturated methyl ketone allowed rapid access to both D-ribo-phytosphingosine and L-arabino-phytosphingosine.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Zaed, Mr Ahmed Mohamed and Sutherland, Professor Andrew
• Authors: Calder, E.D.D., Zaed, A.M., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Copyright Holders: Copyright © 2013 American Chemical Society
• First Published: First published in Journal of Organic Chemistry 78(14):7223-7233
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher